Ethyl orthoformate → 6H-Indeno[5,4-d]oxazol-8(7H)-one

HRID 340666Notes

Reaction equation

HRID 340666 reaction equation
Br.[NH2:2][C:3]1[C:11]([OH:12])=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:13])=[CH:5][CH:4]=1.[CH:14](OCC)(OCC)OCC>O1CCCC1.C(OCC)(=O)C>[O:12]1[C:11]2[C:10]3[C:9](=[O:13])[CH2:8][CH2:7][C:6]=3[CH:5]=[CH:4][C:3]=2[N:2]=[CH:14]1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 673534616-Amino-7-hydroxy-2,3-dihydro-1H-inden-1-one hydrobromide

Product 1

HCID 577812656H-Indeno[5,4-d]oxazol-8(7H)-oneYield 362%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Amino-7-hydroxyindan-1-one hydrobromide (50 mg, 0.205 mmol) and triethyl orthoformate (128 μL, 0.769 mmol) were heated under reflux in tetrahydrofuran (2.5 mL) for 0.5 hr. The mixture was diluted with ethyl acetate, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20) to give the title compound (21.9 mg, yield from Reference Example 362%).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→80/20)

Sources & evidence

ORD record
ord-40f48dd0016442b7855ea81bbdc353f3
Source dataset
uspto-grants-2014_11
Patent number
US08895591B2

Reaction notes

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